The Josiah B. Gillespie family of six moved by wagon and horseback from their home at Coxville, near Chadron, Nebraska, to west-central Oklahoma in 1899. Gillespie, forty-nine years of age, a horse fancier and winner of the Chadron-Chicago horse race of 1893, also drove a herd of more than fifty horses to Oklahoma. His reasons for leaving Nebraska are not clear, although poor business conditions were probably to blame. Gillespie's wife, Anna, kept a journal during the fifty-day trip from Nebraska through Kansas to Oklahoma that illustrated the difficulties of travel under such conditions.
"Traveling in a wagon," said Mrs. Gillespie in her first diary entry made on August 17, 1899, "is no doubt a very pleasant way of passing the time when one does not have to do it; but I believe I prefer home after all, especially when [we] must travel whether [one] wants to or not." The party crossed the Niobrara River on August 19, and Mrs. Gillespie noted the presence of wind and rain that seemed to pursue them throughout the trip.
Moving stock such a distance had disadvantages. On August 20 Mrs. Gillespie noted, "Billy [Billy Schafer, the riding horse] was sick this morning; had a spell of cramps, the result of [a] serruptious [surreptitious] visit to a corn field and a too free indulgence in green corn." A colt sickened and died along the way.
On August 25 Mrs. Gillespie reported, "We came over some of the roughest roads I ever saw this morning. In fact, there was little or no road at all-nothing but cow paths. . . . We crossed the Loup five times today." On August 27, a Sunday, the family camped at Brownlee. Several days later the ubiquitous mosquitoes and rain again plagued the travelers. "This is some of [the] romance of traveling," said Mrs. Gillespie on August 31. "We are well provided with rubber blankets and shakers but as usual they could not be found. We are going to move on this morning, although it is still raining."
In early September for ten days the Gillespies visited in the Ord-Scotia-St. Paul area, where they had lived before moving to Dawes County. September 16 found them near Grand Island, afflicted by rain and mosquitoes "as large as grasshoppers." The party continued south through Hastings, Nelson, and Superior.
On September 20, 1899, the family crossed into Kansas. By October 4 they were in Oklahoma Territory. Mrs. Gillespie's last entry, dated October 12, reported their crossing of the Cimarron River on the way to visit the family of her sister at Hitchcock. The Gillespies then moved on to Kingfisher and later to Fay.